


50 Kisses (Critical Role Version)

by celtoreo



Category: Critical Role (Web Series)
Genre: Adorable Jester Lavorre, Caleb Widogast Deserves Nice Things, Caleb Widogast is a Mess, F/M, Fluff, Kissing, Lonely Essek Thelyss, M/M, Mollymauk Tealeaf Lives, Public Display of Affection, Waltzing, hot boi
Language: English
Status: In-Progress
Published: 2020-03-26
Updated: 2020-03-26
Packaged: 2021-02-28 20:27:34
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,182
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23323177
Author URL: https://archiveofourown.org/users/celtoreo/pseuds/celtoreo
Summary: I take a list of prompts I found on tumblr and meticulously respond to each one. I will put the next kiss I will be writing in the notes of each chapter, so feel free to suggest ships for them when it comes around. Some can be familial/platonic relationships, because there's nothing wrong with kissing your homies- but some may be abusive. I will tag it when it comes up.Refamiliarizing myself with sporadic amounts of fluff and angst and familiarizing myself with writing these characters. Each chapter should be ~500-750 words unless I really get excited about something.I will try to post weekly lol- but no promises.
Relationships: Essek Thelyss/Caleb Widogast, Jester Lavorre/Caleb Widogast, Mollymauk Tealeaf/Caleb Widogast
Comments: 1
Kudos: 39





	1. a public kiss (widojest)

**Summary for the Chapter:**

> They dance. One step, two step, three step, four. To anyone else, the music would get old- but not to Caleb. Not with Jester in his arms.

**Notes for the Chapter:**

> Soft Caleb and Jester rights. They dance, and Jester's sweetness flusters Caleb. 
> 
> next chapter: a kiss out of greed (widomauk)

Jester tugs Caleb by the hand toward the dance floor, and he can do little but stare and follow. Her skin is cool to the touch, soft and familiar, her freckled arm extended as she leads him on. She's wearing a stunning dress that reminds him of the sunset over a field he walked through with Nott, once, except she's much more beautiful than that. His heart feels strangled in his chest. This isn't the first time they've danced, but this feels different, for some reason. He hasn't been able to take his eyes away from her for the whole night. 

"Come on, Caleb!! The song is starting!" she fusses, suddenly and quickly sweeping herself close to him, putting her free hand on his shoulder. He quickly snaps to focus again, sheepishly fumbling to place his hand on her hip. When he looks down at her, lips already moving to form an apology, she smiles and lets out a laugh before resting her head on his chest. He can practically feel the plushness of her hair, even though it's not making any actual contact with him, and it makes him forget what he was going to say.

They dance. One step, two step, three step, four. To anyone else, the music would get old- but not to Caleb. Not with Jester in his arms.

"I think this is pretty great, don't you, Caleb?" she asks softly, eyes closed as they steadily and gently move. He hums is agreement, just watching her gently, and she lifts her head to blink big, deep violet eyes up at him. "Are you sure? You have been pretty quiet this whole time," she says, voice suddenly becoming concerned. He blinks, and then quickly nods, giving a small, hesitant sort of smile.

"Ja, I am alright, Jester. This is just a nice night, no need to ruin it with my prattling," he says softly, lifting his hand to brush her hair from her face, and the little blue tiefling scoffs, lifting her head. 

"I like it when you talk! You're so smart, and funny, and you have a nice accent," Jester lists, and it seems like she's going to go on, so he smiles a little bigger. 

"Is that so, mein Schatz?" he asks, and she giggles delightedly, poking his chest. 

"Yes! See! You did it right there! Look how wonderful!" she insists, and with hardly a glance around, he quickly realizes they have an audience. A heat starts to spread across his face and he takes a breath as she continues. "You talk so pretty, Caleb. You know? Mein Schatz. Oh wait-- I hope that doesn't mean shit-"

"It doesn't," he laughs sheepishly, and the heat brightens to a burn. Jester's eyes widen further and she squeals- they have yet to miss a step, but he's sure he will if he keeps looking at those pretty eyes any longer.

" Caaaaleebbb!! You're blushing! Ooh- tell me what it means, tell me what it means! " she giggles, and then gasps. "Oh! I know, does it mean-" His heart is pounding too loud in his chest, too fast. He can feel way too many pairs of eyes on them and it makes him nervous, and Jester is talking so loudly he swears the Wildmother herself would be able to hear it. She's listing things and he can barely hear them, but he just leans forwards and touches his forehead to hers and she stops, freezing entirely. They're not dancing anymore, but the music is still playing.

"Mein schatz," he whispers, softly. He can feel her breath against his lips- it's slower, softer, and colder than his. "It means my treasure. Or sweetheart." 

He's not sure who moves first, but suddenly Jester's lips are on his, and they're just as soft and cool and familiar-feeling as her hands are. And he can't pull away- he just relaxes, forgetting the music and the practiced dance and the dancing people around them- and focuses on just Jester.

His sweetheart. 

**Notes for the Chapter:**

> Soft Caleb and Jester rights. They dance, and Jester's sweetness flusters Caleb. 
> 
> next chapter: a kiss out of greed (widomauk)


	2. a kiss out of greed (widomauk)

**Summary for the Chapter:**

> "Oh, come on, Caleb. The book can wait for a few more minutes. It doesn't have feelings. I do, and I cannot," the purple tiefling purrs languidly, sprawled out across the bed and watching Caleb carefully. The human man hasn't paid him a mite of attention for at least the last hour and it's beginning to get on his nerves. His pretty spells and all that mess.

**Notes for the Chapter:**

> Mollymauk likes attention from Caleb. He intends on keeping it for as long as possible. 
> 
> next chapter: a kiss as an apology (shadowgast)

"Oh, come on, Caleb. The book can wait for a few more minutes. It doesn't have feelings. I do, and I cannot," the purple tiefling purrs languidly, sprawled out across the bed and watching Caleb carefully. The human man hasn't paid him a mite of attention for at least the last hour and it's beginning to get on his nerves. His pretty spells and all that mess. 

He sighs, lifting his head from where he hangs upside down off the edge of the bed and sitting upright. Then, promptly, he falls and lays on his front dramatically, tail flicking as he lets out a sulky growl. Cursed wizards. Always on the pursuit of knowledge rather than the pursuit of good and proper things like attention or cuddles or Mollymauk. He'd even tried to entice the Zemnian by removing his coat. Alas, it was to no avail- Caleb had not glanced up once from his reading. 

But then he feels a sudden, warm, familiar touch to his lower back, the place above the base of his tail. He lifts his head and brings his arms out in front of him, raising his brows as he props himself up on his elbows. Then he turns over a shoulder to look, and he meets burning blue eyes that immediately bring a smile to his lips. 

"Fine," Caleb whispers, and Mollymauk turns to sit upright and face him, bringing their faces closer. "Five minutes." The tiefling grins, taking Caleb's hand and gently resting it on the small of his back. Molly lifts his to cup Caleb's face, watching the way the man's pupils dilate as his breath spills over his lips. He smiles further.

"Then I will do my best to make those five minutes powerful," he croons, and leans forwards to catch Caleb's lips, already eager and willing to give him his everything. He must succeed, because by the time Caleb pulls away, it's been at least twenty minutes and Molly's shirt has *somehow* been a little bit more undone. He also is aware that both he and Caleb now have a few new colors on the sides of their necks. He puffs a breath through his nose when Caleb's lips leave his skin.

"I should get back to work now. Spells do not learn themselves," he says, like he's not on all fours over Mollymauk. The tiefling quirks his brows and lifts his hands to stroke them through Caleb's hair, giving a smirk. 

"Yes, but spells can always be learned later," he reminds him, leaning up to take another kiss from what's happily his. And then another, because he can't help it. And then another because he can- a fourth because he has the power to- a fifth Caleb gives him. The sixth he takes, because he can happily say he is a greedy bastard when it comes to Caleb Widogast- and he starts to lose count from there.

**Notes for the Chapter:**

> Mollymauk likes attention from Caleb. He intends on keeping it for as long as possible. 
> 
> next chapter: a kiss as an apology (shadowgast)


	3. a kiss as an apology (shadowgast)

**Summary for the Chapter:**

> "There's no need to be so hostile, Widogast. I've the same conclusion that you have," he says, keeping his voice cool, measured. He leans for his pack, pulling out a mirror that he lifts to catch his own reflection in. He acts like it's to fix his own hair, but it's actually just to keep an eye on the fire-wielding wizard. His blue eyes haven't left him yet. Blue, blue, blue.
> 
> "And what's that?"
> 
> "That this won't work."

**Notes for the Chapter:**

> MILD SPOILERS from i believe c2e96- correct me if i am wrong! Its never directly stated but heavily implied. 
> 
> Essek has things he needs to apologize for. And as it turns out, Caleb thinks the same of himself.
> 
> I might continue this one later- feels rushed and I want to write an Essek apology.   
> next chapter: a kiss on a falling tear (jester x yasha)  
> Taking suggestions for 'a kiss goodnight'! Please deposit the ships you'd like to see written for that one in thd comments below :)

The tension between them is palpable, and Essek has learned he hates it much more than many other things. It's a pit in his stomach that's replaced the warmth and safety that once sat in his chest whenever he was around Caleb. A lump in his throat that he can't swallow, no matter how much he tries. He knows Jester was only trying to help them by putting them on watch together, but the other wizard hasn't looked at him once, and it's starting to give him a headache. The red light his eyes cast through the darkness of the night barely reaches the edge of Caleb's shoulder, even though Jester had intentionally put their bedrolls quite close. He's moved away from him, inch by inch, slow enough that no one who's not paying attention would notice. 

But he does. He's paid a lot of attention to Caleb since it all happened. Not intentionally- sometimes his gaze just drifts to him and he has to meet those blue eyes and pretend the accusatory voice he's so fond of using doesn't just _get_ him sometimes. Not that he feels guilty- he knows what he's done, and he knows that he can't expect forgiveness from Caleb.

It still hurts when he uses the word 'friend' like a knife.

He's about to look away, but then stunningly blue eyes meet his. His heart quickly spasms and he turns his head away, pressing his tongue into the inside of his cheek.

"What is it, Essek," Caleb says in that too high, too false, too flat voice of his that he always uses when he's attempting to patronize him. "Do you see something you like?"

He swears that this conversation had been so much more friendly before. Maybe it was because Jester was there. But Caleb had told them that they were hardly different- a mirrored reflection of one another. It had become clear that the wizard saw him as the dark side. He had told him, too, that the toxin in his veins was something that had been taught to him, rather than something that he had been born with. Maybe it was because he had yet to see the fangs on the spider.

"There's no need to be so hostile, Widogast. I've the same conclusion that you have," he says, keeping his voice cool, measured. He leans for his pack, pulling out a mirror that he lifts to catch his own reflection in. He acts like it's to fix his own hair, but it's actually just to keep an eye on the fire-wielding wizard. His blue eyes haven't left him yet. Blue, blue, blue.

"And what's that?"

"That this won't work. Whatever Jester is trying to do. Whatever I'm trying to prove by staying with this party. Whatever I'm doing here," he murmurs, snapping the mirror closed. He then tucks it into his pack and rises, bending back over to pick up his bedroll and move it away from Caleb's. He sees Caleb's lips twitch and he shakes his head, continuing. "Don't worry. I will be leaving after I say goodbye to everyone in the morning." 

There's a pause. The fluttering anxiety in his stomach only intensifies as he lays his bedroll back out and sits upon it. 

"I did not ask you to leave, Essek," Caleb says, and something in the Shadowhand's throat tightens and snaps.

"Then what do you want me to do? I'm trying, Caleb. I do not expect to regain your trust so easily, but I am trying," he says, ignorimg the tears that burn in his eyes stubbornly. He looks off into the darkness, rather than at the human man, and he knows that Caleb can hardly see him now that his eyes are turned away.

"I know. I can tell. I just do not understand why you didn't tell at least me any of this before," the wizard's accented voice rumbles, quiet and soft. " we were very close, you and I. Closer than the others believe. "

"Jester believes it," Essek says dully, lifting his hands to wipe his eyes. "But we aren't like that anymore. Are we?" The pain in his chest almost feels like it's growing permanent. He doesn't want it to be true, but he feels like he's never going to escape this. Not even if he flees to across the world, he will never escape the pain of the fading embers of feeling that Caleb's left unstoked in his heart.

It's quiet again, and Essek starts to think that maybe Caleb has chosen to ignore him, but then warm fingertips grasp his chin and he can do nothing else but look up at the wizard's scruffy face. He stares unflinchingly, even as a tear that he did not want to allow slips down his cheek. Caleb's thumb lifts and wipes it away.

"I'd like to think we could be that again," he says quietly, voice in that low, rumbling tone he only uses when he really means it. Essek lets his composure crumble and his breath hiccup, and Caleb sinks down before him, ever so softly touching his forehead to his. "Do you think so?"

"I've begun to think we might never be able to. I don't know why you still can bear to be around me. I can't even look at you without-" he's going to say something else. He's going to go on and on about how much he likes looking at Caleb but how much Caleb must hate looking at him. He's going to tell him that what he's doing is pointless and worthless because nothing will ever change, but then the distance between them is suddenly closed and Caleb is kissing him.

He doesn't pull away- in fact, he reciprocates it- lifting a hand to rest it on Caleb's shoulder and letting his eyes fall shut. It feels different than all of the kisses that came before. Softer, sadder- but something about it is genuine and true. Like a... Like an apology. The thought barely has time to crest before Caleb pulls away again.

"I'm sorry this has happened," he whispers, blue eyes pained. Essek believes him.

**Notes for the Chapter:**

> MILD SPOILERS from i believe c2e96- correct me if i am wrong! Its never directly stated but heavily implied. 
> 
> Essek has things he needs to apologize for. And as it turns out, Caleb thinks the same of himself.
> 
> I might continue this one later- feels rushed and I want to write an Essek apology.   
> next chapter: a kiss on a falling tear (jester x yasha)  
> Taking suggestions for 'a kiss goodnight'! Please deposit the ships you'd like to see written for that one in thd comments below :)


End file.
